Vat dyestuffs of the anthraquinone series



Patented Sept. 20, 1932 UNITEDSTATESPATENT- OFFICE x o'rro BAYER, or manxronr onqlrnn-ivmm, GERMANY, AS$IGNOR r GENERAL ANI- LINE wonxs, INC, on NEW YORK, N. Y., A CORPORATION or DELAWARE VAT nvns'rurrs on THE ANTHRAQUILTONE SERIES No Drawing. Application filed October 28, 1931, Serial No.;57 1,683, and in Germany November 7, 1930.

My present invention relates to new vat dye-stuffs and more particularly to thosecor responding to the general formula B nei-c041 wherein R means a radical of the anthrasolvent of high boiling point. Acid-binding agents may be also added.

The new vat dyestuffs yield yellowish dyeings of satisfactory fastness properties. In intensity and affinity for cotton, they surpass the analogous dyestuffs obtained by starting from other aromatic carboxylic acid halides.

In order to further illustrate my invention the following examples are given, the parts being by weight and all temperatures in centigrade degrees, but it is however to be understood, that my invention is not limited to the particular products nor reacting con:..

ditions mentioned therein.

Example 1 22 parts of l-amino-anthraquinone are dissolved in about 500 parts of boiling ortho-dichloro-benzene. The solution is mixed during a short time with 22 parts of diphenyl- 4-carboxylic-acid-chloride. When the evolution of hydrochloric acid has ceased (after about half an hour) the yellowish brown solution is allowed to cool. The dyestuff precipitated in yellow crystals is filtered ofi and washed with alcohol. the formula:

It corresponds to diphenyl-l-carboxylic acid chloride by the equivalent amount of the anhydride of diphenyli-carboxylic acid.

By starting from 25 parts of 1-amino-6- (or 7-) chloro-anthraquinone instead of 22 parts of l-amino-anthraquinone a more reddish dyeing compound is obtained.

I I m rz z H I Into a solution of '34 parts ofl-amino-5- benzoyl-amino-anthraquinone inabout 700 parts of trichloro benzene, 21 parts of diphenylA-carboxylic-acid chloride are introducedat 180 C, while stirring. WVith an intense evolution of hydrochloric acid the formation of the dyestufl? is complete in abouthalf an hour.

The dyestuff which. crystallizes already in the hot is filter'ed at i about 50 C. and washed with alcohol. The i 5 benzoyl amino 1 (diphenyl 1 carboxyl-i amino) anthraquinone of the formula dyes froma claret red cold or hot vat clear full yellow shades which surpass thatob- I the formula v Example 3 I A mixture of 25 parts of l-aminomethoXy-anthraquinone, 500 parts of nitrobenzene, 3 parts of'collidine and 23 parts ofdiphenyl-a-carboxylic acid chloride is heated to 190 C. for about half anhour. Wlijen cool"- the dyestufi which is precipitated in red crystals is filtered, washed with alcohol and dried. It corresponds to the formula I claim:

1. As new compounds the vat dyestufis I of the general formula R NH GO R (wherein R means a radical of the anthraquinone series and R a radical of the diphenyl series), which compounds dye cotton and Wool from the vat yellowish shades.

2. As a new compound the vat dyestuff of the formula which; compound represents yellow crystals melting'at 254, dyeing cotton and wool from a-bluishred vat very-clear intense greenish yellow shades of a very good fastness.

In testimony whereof, I affix my signature.

- OTTO BAYER.

and dyescotton from'an orange vat very bright yellowish orange shades.

By replacing l-amino l-methoxy-anthraquinone by 34 parts of t-amino-l.2 -phenylimidazole-anthraquinone a new 'dyestufl is obtained which dyes from a-brownish redvat fast yellowish orange shades. 1

12 parts of the reduced condensation product prepared from 5-nitro-anthraquinone-2- carboxylic acid chloride'and 1-amino-5 benzoyl-amino-anthraquinone aremixed with 4, 5 parts of diphenyl-4-ca-rboxylic acid chloride at'200 C. in about200 parts of trichlorm benzene. The mixture is stirred-until the evolution of hydrochloric acid has. ceased. The dyestuff precipitated ingolden yellow crystals dyes from a claret'redvat intense greenish yellow shades. It corresponds to As further derivatives of l-amino-anthraquinone which are suitable for the present process may be named: diamina-dianthri- Inides and their derivatives containing a carbazole nucleus and aminoanthraquinone-1.2- acridones. 

